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Counterfeiting in Performance

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Counterfeiting in Performance Drug Testing Research Article and Analysis Received: 10 February 2009 Revised: 16 April 2009 Accepted: 16 April 2009 Published online in Wiley Interscience: (www.drugtestinganalysis.com) DOI 10.1002/dta.30 Counterfeiting in performance- and image-enhancing drugs Michael R. Graham,∗1,2 Paul Ryan,1 Julien S. Baker,2,3 Bruce Davies,2 Non-Eleri Thomas,4 Stephen-Mark. Cooper,4 Peter Evans,5 Sue Easmon,6 Christopher J. Walker,7 David Cowan7 and Andrew T. Kicman7∗ The current drastic escalation in obesity may be contributing to the exponential rise in drugs used for image enhancement. Drugs such as anabolic-androgenic steroids (AAS) are perceived as a viable method of achieving a perfect physique. They are also the most widely abused drugs in sport. The Internet has encouraged the abuse of expensive drugs, particularly human growth hormone (hGH), resulting in increased importation for personal use. The substantial increase in this market has opened up avenues for counterfeiting, estimated as a multi-million pound business. The acute adverse effects from contaminated vials may result in a variety of pathologies including communicable diseases. In 2007, in the UK, a series of intramuscular abscesses, requiring surgical treatment, led us to study samples obtained from the underground market. The analysis of 38 parenteral samples and 19 oral samples of tablets was performed by a World Anti-Doping Agency (WADA) accredited laboratory, in an attempt to establish the extent of available counterfeit products. Fifty-three per cent (20) of the injectable AAS esters and 21% (4) of the oral tablets were counterfeit. Culture and sensitivity revealed the presence of skin commensal organisms, which may have contributed to the development of the abscesses. Users of AAS and hGH for sport, including bodybuilding, are currently risking their health because of counterfeit and poorly controlled products. Copyright c 2009 John Wiley & Sons, Ltd. Keywords: AAS; abscess; cosmesis; image; performance Introduction and image-enhancing drugs by female athletes; this has led to an assessment of the type of drugs they use.[3] Yearly reports from the World Anti-Doping Agency (WADA) A recent doping violation, contravening the WADA code, has demonstrate that anabolic-androgenic steroids (AAS) are the most illustrated the excessive ‘‘polypharmacy’’ in the athletic world, [4] abused group of drugs in competitive sport, despite enormous which is believed to be the tip of the iceberg. A letter sent to advances in detection techniques and severe penalties for positive The Times newspaper identified the doping regime of Mr Dwain test results. Chambers, a disqualified international athlete, who admitted [4,5] Several countries, including Australia, Argentina, Brazil, Canada, taking combinations of prohibited substances. the UK and the US have legislation to control AAS. Nevertheless, AAS are readily obtainable from many sources worldwide. Many countries permit the sale of AAS without a medical prescription[1,2] ∗ Correspondence to: Michael R. Graham, Newman Centre for Sport and Exercise and sale of these products to overseas customers is also not Research, Newman University College, Birmingham, UK. restricted. This sale is made easier because of the Internet and e- E-mail: [email protected] mail. Most AAS found in Europe originate not only from countries ∗∗ Correspondence for drug analysis to: A. T. Kicman , Drug Control Centre, King’s within the European Union and Russia but also from Thailand, College London. E-mail: [email protected] Turkey, Egypt, India and Pakistan.[2] In the US, significant quantities of AAS emanate from Mexico, as well as from Russia, Romania, 1 The Newman Centre for Sport and Exercise Research, Newman University College, Birmingham, UK and Greece.[1] In the UK, AAS and recombinant human growth hormone (rhGH) are controlled under Schedule 4, Part 2 of the 2 Health and Exercise Science Research Unit, University of Glamorgan, MisuseofDrugsAct1971.Thereisanexemptionfromrestrictionon Pontypridd, UK the possession of these substances, when they are in a medicinal 3 Division of Sport, University of West of Scotland, Glasgow, UK product and are for self-administration. As a consequence of this legal control, AAS can only be obtained in the UK for non-medical 4 Cardiff School of Sport, University of Wales Institute, Cardiff, UK usefromsourcesofunknownprovenance,suchastheblackmarket or the Internet. These products are not necessarily produced in 5 RoyalGwentHospital,Newport,Gwent,UK accordance with Good Manufacturing Practice, as would be the 6 Kingston University, Penrhyn Road, Kingston upon Thames, Surrey, UK case with licensed medicines obtained from legitimate sources. Of 135 particular concern is the use of anabolic steroids as performance- 7 Drug Control Centre, King’s College London, UK Drug Test. Analysis 2009, 1, 135–142 Copyright c 2009 John Wiley & Sons, Ltd. Drug Testing and Analysis Michael R. Graham et al. ◦ The use of performance-enhancing drugs is contrary to all temperature, 320 C, was held for 5 min. Injections (1 µL) were Olympic values and creates negative role models for young made in the splitless mode; the injection port and transfer line ◦ athletes. Peer influence and the information that AAS administered temperatures were 250 and 280 C, respectively. Helium was used byintra-muscular(IM)injectionare‘lessharmful’thanoralproducts as the carrier gas and the flow rate was 0.7 mL/min. For screening has increased the use of IM preparations. The escalation in the purposes, the mass spectrometer was operated in the selected frequency of IM abscesses in a cohort of bodybuilders in 2007, ion monitoring mode (SIM) using an ion specific for the mono or seen by one of us (MRG), was considered to be as a result of the use bis-trimethylsilyl (TMS) derivative for each compound. The details of non-sterilized or contaminated counterfeit products obtained are summarized in Table 1. from the black market. These abscesses led to an analysis of the Full scan analysis (mass range m/z 80–650) was used for current injectable, transdermal and oral performance- and image- identification of the compounds detected. The chromatographic enhancing drugs (PIED) presently being used by competitive conditions are described above. bodybuilders in the UK. LC-MS/MS analysis of thyroxine Materials A tablet from a bag labelled ‘levothyroxine’ was placed into a tube containing 10 mL of methanol. The contents were mixed Dodecane, potassium hydroxide (KOH), anhydrous sodium sulfate thoroughly by sonication and centrifuged at 1320 g for 5 min. and hexane, all analytical reagent grade, and high-performance Then 0.8 mL of the supernatant was taken and diluted to 5 mL with liquid cromatography (HPLC)-grade methanol and cyclohexane methanol : water containing 0.1% formic acid (70 : 30). A solution were purchased from Fisher Scientific (Loughborough, UK). Am- containing 1 µg/mL of thyroxine was prepared in methanol : water monium iodide (NH4I) and formic acid (Analar, BDH) were containing 0.1% formic acid (70 : 30). A portion of these solution purchased from VWR International (Lutterworth, UK). N-Methyl-N- was transferred to autosampler vials and analysed by LC-MS/MS. trimethylsilyl-trifluoroacetamide (MSTFA), pyridine and methoxy- Chromatographic separation was performed on an Waters Acquity lamine hydrochloride, methyltestosterone, 19-nortestosterone, UPLCsystemusingaZorbaxEclipseXDB-C18column(50×2.1 mm, ◦ 19-norandrost-4-ene-3,17-dione, norethisterone, testosterone, 1.8 µm particle size) heated to 35 C. The mobile phase consisted androst-5-ene-3β,17β-diol, androst-4-ene-3,17-dione and levo- of 0.1% formic acid (v/v) (solvent A) and methanol containing 0.1% thyroxine were purchased from Sigma-Aldrich (Poole, UK). Purified formic acid (v/v) (solvent B). A gradient was employed starting at water was obtained from ELGA Purelab Maxima (Vivendi Wa- 2 30% B, increasing to 55% B in 2 min and to 75% B in 8.66 min ter Systems, High Wycombe, UK). [16,16,17- H3]-Testosterone and returned to the initial conditions in 9.3 min and allowed to (d3T) was purchased from LGC Promochem (Teddington, UK). equilibrated for a further 0.7 min. The flow rate was 0.25 mL/min. Androst-5-ene-3 ,17 -diol, 19-norandrost-4-ene-3 ,17 -diol and β α α β The injection volume was 10 µL. 19-norandrost-4-ene-3 ,17 -diol were purchased from Steraloids β β This was coupled to an Applied Biosystems API 3200 triple (Newport, RI, USA). Mesterolone, methenolone and methenolone quadrupole mass spectrometer with a Turbo Ionspray source enanthate (Primobolan-Depot) were obtained from Schering Ger- operating in the positive ion mode. The optimized source many. DHEA, Sustanon 250 (testosterone propionate, testosterone ◦ conditions were source heater probe temperature 500 C, Turbo isocaproate, testosterone phenylpropionate and testosterone Ionspray voltage 5500 V, curtain gas setting of 15 psi, collision gas decanoate), Durabolin (nandrolone phenylpropionate) and Deca- setting of 6, ion source gas 1 setting of 45 psi, ion source gas 2 Durabolin (nandrolone decanoate) were obtained from Organon. setting of 50 psi, declustering potential of 65 V, entrance potential Clenbuterol sulphate was obtained from K. Thomae. Clostebol of 10 V, cell exit potential of 51 V, and collision energy of 35 V. acetate was obtained from Farmitalia. Methandienone was ob- The mass spectrometric method was set up to detect the ions tainedfromCIBA.StanozololwasobtainedfromSterling-Winthrop. (mass range m/z 500–780) produced by after collision induced Boldenone was kindly donated by Professor Don Catlin of UCLA. + dissociation of m/z 777.2, the protonated molecule [M+H] , (product ion scan). Methods The tablet extract gave a peak consistent with the retention times (4.68 min) and product ion spectrum for thyroxine. The The generic name of the drug was identified from the brand name, protonated molecule was visible at m/z 777 and collision induced specified on the label. If more than one drug of the same generic dissociation resulted in the formation of m/z 731, 634 and 605 are [6] formula was analysed, they were provided by different individuals consistent with those reported previously.
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